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$3,149,000
2 Beds 3 Baths 621277 MLS
Just three homes from the bay, this waterfront home in Islamorada offers beautiful bay views, quick boating access and the quintessential Florida Keys lifestyle. The open 2 bedroom, 2 bath upstairs features bay views and high-end finishes. The outdoor offers spacious multi-level terraces with over 4000 sq ft of paver tiles and a waterfront tiki hut perfect for relaxing or entertaining. Boaters will appreciate the concrete dock with 5' draft, davits and fish-cleaning station, with quick and easy access to the bay and to the ocean via Tavernier or Snake Creek. Impact windows and doors, remotely operated roll-down shutters, gated entry, 3rd bathroom downstairs with storage and covered parking. Ideally located in Planation Key Colony; close to shopping, dining, entertainment and healthcare.

114 N Coconut Palm Blvd, Tavernier

$14,000,000
5 Beds 4 Baths 621096 MLS
The most sought-after bay in all the Florida Keys, and one of the largest properties on it. This true double lot spans 1.3 acres with more than 250' of bayfront facing due west for the perfect nightly sunset. A white sand beach transitions into the clear bay waters, while a protected basin offers a 20,000 lb. lift accommodating up to a 40' boat and a 3,000 lb. skiff lift. Ultra-private, with no neighbors in sight and expansive green lawns throughout. The home is sophisticated yet inviting, with an incredible attention to detail throughout and a distinctive blend of Tuscan Mediterranean architecture and classic Keys styling. Enter through the gates into a private courtyard and open-air atrium with freshwater ponds and fountains. An elevator provides access to the second floor, where a one-of-a-kind living room overlooks the bay with exposed wood beams and tongue-and-groove ceilings. Updated throughout while preserving its original ornate finishes, this level flows from the living and dining rooms into the kitchen with a gas range and dumbwaiter. The bayfront primary suite features an impressive bath with dual vanity areas. Two additional bedrooms share a Jack-and-Jill bath, plus a half bath finishes off the second floor. Halfway down the main staircase is the entrance to one of the favorite rooms in the home: the library. With vaulted ceilings and a fireplace, it is the ultimate setting to work, relax with a good book, or serve as a fifth bedroom. The ground floor offers a separate ensuite guest bedroom, garage with front and rear doors, laundry room with double washers and dryers, and an outdoor kitchen. Outside, a massive 40' x 22' pool features a hot tub and beach-entry shelf. Extensive uplighting and downlighting illuminate the property at night. An additional front lot includes a detached structure currently used as a gym and storage. A once-in-a-lifetime opportunity to own one of Islamorada's most prized bayfront estates.

350 Buttonwood Bight Ln, Tavernier

$499,900
2 Beds 2 Baths 620763 MLS
Welcome to Summer Seas, a desirable waterfront community in the heart of the Florida Keys! This beautifully maintained 2-bedroom, 1.5-bath condominium offers the perfect blend of comfort, convenience, and island living. Enjoy a bright and inviting layout with an open living area, comfortable bedrooms, and a private balcony to relax and take in the tropical surroundings. The community features waterfront amenities, including a marina, pool, and easy access to the beautiful waters of the Florida Keys. Conveniently located near restaurants, shopping, boating, and everything Islamorada and Tavernier have to offer. Whether you are looking for a full-time residence, vacation getaway, or investment opportunity, this charming Keys retreat is ready to welcome you home.

88500 Overseas Highway Unit 208, Tavernier

$6,500,000
3 Beds 4 Baths 620553 MLS
Welcome to your private oceanfront retreat, ideally situated on a quiet cul-de-sac in the heart of Tavernier. Set on an expansive 28,705-square-foot lot, this beautifully renovated estate in 2024 offers breathtaking Atlantic Ocean views and seamless indoor-outdoor living. The open-concept floor plan is designed to showcase the spectacular water views from nearly every room, elevated ABOVE FLOOD for added peace of mind. The property features a 2-bedroom, 2.5-bath main residence and a private 1-bedroom guest suite above the garage, thoughtfully redesigned with interiors curated by acclaimed designer Kevin Gray. Top of the line finishes throughout. Outside, enjoy a stunning resort-style pool and spa, an expansive oceanfront veranda, tropical landscaping, and an exterior lift providing convenient access from the covered carport to the main entrance. For boating enthusiasts, the private dock is equipped with an elevator boat lift and a charming tiki hut, creating the ultimate Florida Keys waterfront lifestyle. Whether you're enjoying sunrise coffee overlooking the Atlantic or heading offshore for a day on the water, this exceptional estate offers luxury, comfort, and timeless coastal elegance.

197 Lowe St, Tavernier

$2,999,000
3 Beds 4 Baths 620411 MLS
Updated canal front pool home located in a desirable neighborhood with quick and easy access to the bay or ocean via Tavernier Creek, a boaters dream. It features a 3 bedrooms, 3.5 bath, a ground level entry with beautifully designed foyer, a large entertainment room with bar, a laundry room and a half bath. The second level has a spacious bedroom with an en-suite bath and an additional room for bedroom or office space with easy access to the pool/outdoor entertainment area. The main living area has an open-concept design with balcony, dining area and updated kitchen along with a guest bedroom and guest full bath. The spacious private master suite is located on the upper level with an en-suite bath, balcony and easy access to roof-top entertaining, which includes beautiful bay views, sunrises and sunsets. Additional interior features include new recessed lighting throughout the house along with interior stair lighting, updated bathrooms and new tile throughout the house, including outdoor balconies. Outdoor features include a beautifully designed entertainment area that includes a new pool with heater/cooler, outdoor shower, a fire pit and brand new outdoor kitchen with tiki, which makes it a great area to relax with friends and family after a long day of fishing. A new 70 ft dock with new pilings, Trex Decking and a newly installed 20,000# lift for your boat. Solid concrete construction with a new metal roof, newly waterproof coated/sealed flat roof top, impact windows and doors, new driveway pavers, new privacy fence, low voltage lighting and low maintenance landscaping. An attached air-controlled garage with new hurricane rated garage door and side doors, has plenty of storage for all your toys. This home checks all the boxes whether it's a primary residence, a weekend getaway or luxury vacation rental, it's move in ready. Great location near shopping, schools & restaurants.

111 Spoonbill Rd, Tavernier

$2,899,000
4 Beds 4 Baths 620278 MLS
Exceptional investment and lifestyle opportunity in the heart of Plantation Key. This offering includes a triplex income property together with the adjacent multifamily lot, giving you both immediate rental income and room to grow. In the Village of Islamorada, it is rare to find side-by-side multifamily parcels in such a convenient, desirable Upper Keys neighborhood. 127 Monroe Drive is a concrete triplex of roughly 2,400 sq ft on a 7,500 sq ft lot, with 3 rental units (1/1, 1/1, 2/2), full kitchens and baths, abundant on-site parking, and comfortable outdoor living areas. Units 1 and 3 were renovated with fresh finishes and updated interiors that attract solid tenants and keep maintenance in check. In 2025, the dock electric was upgraded with a dedicated meter for the dock power, one on each property. Next door, 121 Monroe Drive is an additional multifamily parcel of about 7,500 sq ft, now vacant and ready for your next phase of development. Consider adding more units, a pool, covered parking with storage, or enhanced outdoor spaces to create a cohesive compound and boost rental revenue. Multifamily waterfront land in Islamorada is limited, and demand for quality rentals remains strong. With recent upgrades already completed and easy access to the mainland, this combined offering is a great opportunity for investors, 1031 buyers, or owner-operators who want a flexible Keys property with income today and room for future build-out and long-term appreciation. Free access to Founders Park, with sandy beach, swimming pool, boat ramp, playground, tennis, pickleball, walking paths, sports fields, dog park and daily fun activities and regular events.

127 & 121 Monroe Dr Unit 1-3, Tavernier

$26,400,000
7 Beds 10 Baths 620022 MLS
Escape to Palm Paradise, a breathtaking oceanfront estate on 7.64 private acres in Islamorada, offering 369 feet of shoreline and sweeping Atlantic views. Tucked behind gates on Plantation Key, this secluded retreat combines lush tropical landscaping with unmatched privacy for the ultimate island escape. The 8,988-square-foot main residence showcases exceptional craftsmanship and thoughtful design. One wing features a dramatic two-story primary suite with a private office, while the opposite wing includes four additional bedrooms and four bathrooms across two levels. A separate two-bedroom guest house provides extra space for visitors, and a whole-house generator adds convenience and peace of mind. Inside, custom woodwork, coffered ceilings, built-ins, and high-end finishes create a warm yet refined atmosphere. Amenities include a chef's kitchen, wine cellar, private gym, elevator, and seamless indoor-outdoor living spaces ideal for entertaining or relaxing by the water. Resort-style outdoor features include a custom pool, tiki bar, outdoor kitchen, beachside fire pit, putting green, observation pier, and a lighted tennis court with cabana. Convenient access by seaplane, helicopter, or a 90-minute drive from Miami makes travel effortless. Perfect for boating enthusiasts, the estate is near dockage and concierge dry storage options. Located in the heart of Islamorada, Palm Paradise offers easy access to world-class fishing, boating, dining, and the laid-back luxury of the Florida Keys. Offered at $26.4M, Palm Paradise is a rare opportunity to own a private waterfront compound ideal for luxury living, family retreats, or executive escapes.

89505 Old Hwy, Tavernier

$712,999
2 Beds 2 Baths 619924 MLS
EARN $$ and enjoy The Florida Keys! OceanPointe is one of the few resorts that allows Short Term Rentals. Each building in the Resort is undergoing building and common area renovations as depicted in the VIRTUAL pictures of the planned Common Area and building 5 Renovation Project. Some of the buidlings have already undergone Renovations. The planned renovations to unit 5308 in building 5 are pending board approval. Your ultimate rest and relaxation vacation awaits at unit 5308. this pristine and upgraded 2 bedroom, 2 bath condo is in sought after BUILDING 5 at OCEAN POINTE SUITES & MARINA! BUILDING 5 is the closest to the POOL, MARINA and BEACH. Enjoy SWEEPING OCEAN AND MARINA views from one of the two balconies while sipping your morning coffee or tea, and your evening cocktail or mocktail. Nature lover? There is an Osprey nest just a short distance of hundred yards away from the balcony off the Living Room. FULLY FURNISHED Very desirable UPDATED 'D' MODEL unit in BLDG 5 at OceanPointe. Bldg 5 is centrally located near both the pool and marina. The 'D' model features the primary bedroom facing the waterfront and has a private balcony. Professionally updated with high end finishes, including brand new furniture, stainless steel appliances, quartz counter tops, new luxury vinyl plank floors, IMPACT Doors and Windows. OceanPointe is directly on the Atlantic side of the Keys, and features a Private Marina, Private Boat Ramp, Onsite Boat & Trailer Parking, Private Beach, Private Fishing Pier, a huge Pool and Spa, Lighted Tennis and Pickle Ball Courts. OceanPointe is tucked away off US1 and is 1 mile away from Harry Harris Beach Park.

500 Burton Dr Unit 5308, Tavernier

$645,000
2 Beds 2 Baths 619878 MLS
Welcome to Summer Sea Condominium Apt 424, a beautifully remodeled and fully furnished bayfront residence in the heart of Islamorada. This turnkey, 2-bedroom, 2-full bath condominium offers 1,148 square feet of light-filled living space with open water bay views from an oversized double-width balcony perched among the treetops on the top floor. Designed for both comfort and entertaining, the open-concept floor plan features a spacious living area, modern kitchen, generous storage throughout, and a custom wet bar with a second refrigerator -- ideal for boating and fishing enthusiasts. Both bedrooms are well-appointed and offer comfortable accommodations for owners and guests alike. Summer Sea is a gated waterfront community known for its beautifully maintained grounds, welcoming residential atmosphere, and outstanding amenities. Residents enjoy two swimming pools including a large heated pool, sandy beach area, fitness center, game rooms, community gathering spaces, elevator access, and breathtaking sunset views over Florida Bay. This community has successfully completed its milestone inspection and continues to reflect exceptional pride of ownership with numerous recent improvements, including 2 new elevators, composite dock, remodeled poolside bathrooms, and storm-rated windows and more-- all completed with no special assessments. Whether you are seeking a full-time residence, weekend retreat, or investment opportunity, this exceptional bayfront condominium captures the very best of the Islamorada lifestyle.

88500 Overseas Hwy Unit APT 424, Tavernier

$700,000
2 Beds 2 Baths 619480 MLS
TOP FLOOR oceanfront living awaits in this beautifully updated 2-bedroom, 2-bath condo located in desirable Sea Gulls development in Plantation Key. Enjoy breathtaking Atlantic Ocean views from the main living area, primary suite, and an expansive private balcony, perfect for soaking in stunning sunrises and refreshing ocean breezes. The tastefully renovated interior is offered turnkey, fully furnished, allowing for immediate enjoyment as a full-time residence or the ideal vacation retreat. Sea Gulls is a gated, resort-style oceanside community offering exceptional amenities, including an oceanfront pool, sandy beach, kayak and paddleboard storage with launch access, chickee huts, outdoor grilling areas, and a fully equipped renovated oceanfront fitness center and a spacious clubhouse featuring a kitchen and game room. Residents and guests are welcomed through an interior foyer with elevator access and beautiful oceanviews. Experience the best of the Florida Keys lifestyle in this exceptional oceanfront offering.

200 Wrenn St Unit 606, Tavernier

$625,000
2 Beds 2 Baths 619284 MLS
Elevated direct oceanfront living from a 5th-floor 2 bedroom 2 bath residence in Sea Gulls on Plantation Key in Islamorada. This all concrete building offers peace of mind and stunning Atlantic Ocean views from a full-length private balcony that spans the entire unit, providing water views from every room. The renovated interior is offered turnkey and ready for immediate enjoyment, ideal as a full-time residence or vacation retreat. Sea Gulls is a gated oceanside community featuring a resort-style oceanfront pool, lounging area overlooking Atlantic & sandy beach, kayak/paddleboard storage & launch area, chickee huts, outdoor grilling areas, oceanfront fitness center w/dedicated yoga room, clubhouse w/kitchenette & game room. Owners and guests are welcomed through an interior foyer with elevator access w/scenic water views, enhancing both convenience and arrival experience. Enjoy the best of the Florida Keys lifestyle with breathtaking sunrises, refreshing ocean breezes, and exceptional amenities all within a beautifully maintained waterfront setting.

200 Wrenn St Unit APT 510, Tavernier

$699,000
2 Beds 2 Baths 619212 MLS
Enjoy breathtaking ocean views from this beautifully updated 2-bedroom, 2-bathroom top-floor condo, fully furnished, in the highly desirable Ocean Pointe community. Positioned for one of the best views in the building, this unit features a private balcony with access from both the living room and the primary bedroom--perfect for relaxing and taking in the scenery. The spacious primary bedroom offers stunning ocean views, direct balcony access, and an updated en-suite bathroom. Both bathrooms have been tastefully renovated, and updated flooring throughout adds to the clean, coastal feel. Raised ceilings enhance the sense of space, making the unit feel open and bright. The kitchen features granite countertops, stainless steel appliances, and a new refrigerator. Additional upgrades include a new washer and dryer and a tankless water heater for added efficiency and convenience. Impact windows and doors provide peace of mind, and the unit is ready for personal use or immediate rental. Ocean Pointe allowsshort-termm rentals, making this an excellent investment opportunity or vacation getaway. Amenities include a large pool and hot tub, tennis courts, pickleball courts, a pool bar, an on-site restaurant, a playground, a boat ramp, a marina, and a private beach. Conveniently located near the pool and tennis courts, this unit offers the perfect combination of comfort, location, and stunning views. Located in the Florida Keys, this property is ideal as a strong investment opportunity, a second home, or your own private coastal retreat.

500 Burton Dr Unit 2409, Tavernier

$1,495,000
4 Beds 3 Baths 619142 MLS
CANAL FRONT - DIRECT OCEAN ACCESS!! Welcome to 128 Dove, an experience in lifestyle. Coveted by many but enjoyed by a select few, this unique upper Keys location is surrounded by protected land preserving the natural beauty of these beautiful islands! Situated oceanside at MM94, this dream maker home offers 2 levels of comfort, exceptional location near sought after Islamorada plus direct ocean access to Rodriguez Key and the famed offshore fishing haunts of the area. The cut in dock basin complete with a 10k boat lift makes those days on the water a breeze. Coastal luxury is the theme on the main level from the kitchen's granite counters and stainless-steel appliances to the soothing canal side primary bedroom. Wake up every morning with the sun sparkling over the water. Enjoy the sea breeze on the screened porch, a perfect way to start your day! The custom walk-in closet (could revert to a bedroom) is sure to please! Working from home? Enjoy a canal side office with views most only dream of! The main level also boasts 2 lovely, updated bathrooms as well as ample pantry storage. Entertaining family or friends? The lower level with its own private access is ready for guests with a super comfy living/dining area, a bedroom and bath plus a convenience kitchen with tons of additional storage. Leading right out to the chickee lounge and patio area, this lower level is perfect for all of your entertainment desires. Oh, and did I mention there is plenty of parking space for 6 cars plus a boat trailer or an RV (with external power already installed). With so much to offer, the super well-maintained home should be at the very top of your must-have list! Come and see for yourself before someone else lives this dream!

128 Dove Ave, Tavernier

$529,999
2 Beds 2 Baths 618934 MLS
Immerse yourself in the highly desirable Ocean Pointe Development offering an unparalleled lifestyle with stunning sunrises and an array of amenities, including NIGHTLY RENTALS! This meticulously maintained 2 bedroom, 2 bathroom condominium offering a new air conditioner, washer, dryer, refrigerator and dishwasher, plus new impact windows and doors and offers a rich history of successful short-term rentals. Discover the allure of this community, highlighted by a protected marina that provides direct ocean access and a convenient boat ramp. The complex features a Jr. Olympic size pool complemented by a 14-person spa, creating the perfect setting for relaxation. Indulge in the exclusive amenities, including an oceanfront café and lounge with an area underneath inviting you to enjoy the serenity of the surroundings. Relish in the coastal lifestyle with a pristine beach area, complete with a boardwalk and gazebo. You will appreciate the lighted pickleball and tennis courts. Don't miss the chance to make this Ocean Pointe condominium your home or a great investment property. Embrace the perfect blend of comfort, luxury, and natural beauty in this captivating development. SELLER OFFERS TO MANAGE THE RENTALS FOR 16% FEE..

500 Burton Dr Unit 1210, Tavernier

$500,000
1 Beds 1 Baths 617483 MLS
Premier 1 bedroom unit a stunning open water and pool view off your private balcony. Fully updated with the open concept kitchen open to the dining and living room. Stunning white cabinets and modern bathroom, Tile floors and granite countertops throughout the apartment. Comfortable queen size bed with a pull-out couch in the living room. The perfect place to lounge and enjoy your days! The condominium is right on the bay with two pools (one heated), a beautiful beach area, Marina with a new composite Dock, Fish cleaning stations, Tiki huts with BBQ grills and picnic tables, Remodeled workout room and game room, community room, fabulous sunsets and friendly residential atmosphere. Safe and secure gated community with 2 brand new elevator. Summer Sea is a multi-story residential waterfront condominium with a friendly atmosphere with on-site management. The community has successfully completed its milestone inspection and continues to show pride of ownership with numerous recent improvements, including two new elevators, a new composite dock, newly remodeled poolside bathrooms, and storm rated windows -- all completed with no special assessments. This condominium is on Plantation Key, Tavernier at MM88.5, just north of the famous Marker 88 Restaurant, a 5-star gourmet restaurant with outside bar. Four restaurants within walking distance. Marina is first come, first serve, other restrictions apply. One pet per apartment with no size restriction. NOTE: The apartment is rented January, February and March 2027 so rental income is already in place!

88500 Overseas Highway Unit 320, Tavernier

$799,000
3 Beds 3 Baths 617505 MLS
Stunning Townhome in the Bayfront Gated Community of Sunset Hammock, a quiet and tranquil community offering resort-style amenities and unparalleled Florida Keys living. This beautifully updated 3-bedroom, 2.5-bath townhome includes a 28-foot assigned boat slip, making it perfect for boating enthusiasts. Inside you will find a bright and open layout featuring two en-suite bedrooms, including a spacious primary suite with a private balcony overlooking the serene lagoon. An additional loft space upstairs provides extra room for an office, den, or guest overflow. Enjoy breathtaking Florida Bay sunsets from the community's private marina, one of the best vantage points in town. Sunset Hammock offers exceptional amenities including a boat ramp, kayak racks, on-site boat/trailer storage, pickleball and tennis courts, a private pool, and a welcoming clubhouse. Ideally situated between Key Largo and Tavernier, you're just minutes from top-rated restaurants, shopping, world-class fishing, and incredible diving. Experience the perfect blend of privacy, comfort, and adventure--your Keys lifestyle awaits at Sunset Hammock.

94220 Overseas Hwy Unit 9C and 28' Boat Slip, Tavernier

$640,000
2 Beds 3 Baths 618028 MLS
NEW LOWER PRICE!! This beautiful 2-bedroom, 2.5-bathroom condo offers everything you need for an stress-free retreat or your full-time piece of paradise. Step inside to a light and bright interior filled with upgrades and thoughtful finishing touches. Two screened lanais provide the perfect spot to relax, unwind, and soak in the stunning views of the lush tropical landscaping, sparkling pool, BBQ tiki hut, and the breathtaking Florida Bay sunsets. This condo comes with assigned parking, dockage and ground-level storage, ideal for keeping your fishing and diving gear just steps from your boat, making your water adventures effortless. Located in a prime spot, it's an easy commute to Miami for a quick weekend getaway or an extended stay in paradise. You'll also be close to the best shopping, dining, and nightlife the Florida Keys have to offer. BONUS: Enjoy peace of mind with the state-mandated engineering inspection complete and all restorative work finished. This is a rare opportunity to own a worry-free slice of paradise! Don't wait—schedule your private showing today and experience the best of bayfront living in the Florida Keys!

200 Harborview Dr Unit 101, Tavernier

$1,390,000
2 Beds 2 Baths 616971 MLS
Located on a tranquil canal-front setting in the desirable Plantation Key Colony, this impeccably updated, turnkey ground-level residence offers two bedrooms, two baths, 50 ft of coveted dockage, and boat slip with immediate bay access. Meticulously maintained and ready for carefree island living. The home's concrete, ground-level construction enhances both durability and ease of maintenance, while a fresh, clean aesthetic unfolds inside and out. Recent upgrades and improvements include brand new metal roof, impact windows and doors, new interior and exterior paint, new interior doors, energy efficient appliances, new sewer line, and re-thatched tiki hut. Updates to the attached pull through garage includes new door rollers, lock hardware, and upgraded flooring and wall finishes, all designed to keep the property in turnkey condition. This home is for those who embrace water-based recreation with easy bay and ocean access via Tavernier Creek, a boat slip with ramp through the garage, and new fish cleaning station with electric and water hookup. The voluntary homeowners association offers a bayfront HOA park with a new boat ramp, beach, and picnic area. With its ideal location and exceptional features, this canal home presents a unique opportunity to embrace the vibrant lifestyle of the Upper Keys.

251 Azalea St, Tavernier